The episode was written by
John Swartzwelder and directed by
Rich Moore. The reason for the late broadcast on August 27, 1992 (the season usually ends in May), was because the
Fox network decided to add an additional episode to the season and show it during the summer to become "the biggest network" on television. As a result, the writers, animators, and producers had to work longer hours than normal to be able to finish the extra episode, which became "Brother, Can You Spare Two Dimes?" guest starred in the episode as Homer's brother Herb. The producers liked his performance in "
Oh Brother, Where Art Thou?" and decided to bring him back for this episode. The decision to make another episode with Herb was reached due to many viewers being unhappy about the sad ending to the previous episode "
Oh Brother, Where Art Thou?" (season two, 1991), in which Homer causes Herb to become bankrupt. It was decided that an episode would be created in which he regains his fortune. Cast member
Hank Azaria noted that DeVito was less enthusiastic in his second performance as Herb: "Some people come in and you can tell they kind of regretted doing it. The second time, Danny DeVito was like 'Yeah, yeah, yeah, let's get it over with.' He did a great job, but he didn't enjoy the process." In part because the writers had so many ideas for what Herb would invent, the original script of "Brother, Can You Spare Two Dimes?" ended up being too long at fifty-three pages. During the same time as the voices were being recorded, the writers cut some of the material.
Showrunner Al Jean has stated that Frazier was hard to record, especially him saying the word "excellence" in the title of Mr. Burns' award.
George Meyer, who directed Frazier, commented that he got the pronunciation right after almost 20 takes. Originally, the producers wanted Foreman to appear instead of Frazier, but he was unavailable. The award that Homer received was based on the Emmy Award, but with a statue of Burns instead. At some point during the season,
Todd Flanders's role as the younger brother was switched; before, he had been the smaller of the two, but since this episode, he has been the elder. The scene in which Homer flips on the switch that turns on the Christmas sign was, in contrast to the rest of the episode, created via
animatics. For several years,
The Simpsons used a series of flashbacks to reflect on the scene in which the character is presently talking about. For instance, in this episode, when Marge talks about getting a new washing machine, the camera cuts to the washing machines vibrating wildly. However, when
Family Guy began imitating the same style, the producers stopped the idea soon after. The scene where Homer bemoans Herb's treatment of him to Marge in bed was taken from another episode because they decided to explain the plot a bit more. ==Cultural references==